JP6050810B2 - 底面反射防止コーティング組成物及びそれの方法 - Google Patents
底面反射防止コーティング組成物及びそれの方法 Download PDFInfo
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- JP6050810B2 JP6050810B2 JP2014514162A JP2014514162A JP6050810B2 JP 6050810 B2 JP6050810 B2 JP 6050810B2 JP 2014514162 A JP2014514162 A JP 2014514162A JP 2014514162 A JP2014514162 A JP 2014514162A JP 6050810 B2 JP6050810 B2 JP 6050810B2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940009976 deoxycholate Drugs 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- ORPDKMPYOLFUBA-UHFFFAOYSA-M diphenyliodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ORPDKMPYOLFUBA-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- ZLHVSEPPILCZHH-UHFFFAOYSA-N ethenyl 4-tert-butylbenzoate Chemical compound CC(C)(C)C1=CC=C(C(=O)OC=C)C=C1 ZLHVSEPPILCZHH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- XJTWZSZWOJKDJL-UHFFFAOYSA-N ethyl 2-hydroxy-4-[2-(2-methyl-3-phenylprop-2-enoyl)iminohydrazinyl]benzoate Chemical compound C1=C(O)C(C(=O)OCC)=CC=C1NN=NC(=O)C(C)=CC1=CC=CC=C1 XJTWZSZWOJKDJL-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000007687 exposure technique Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ULHAZGTYRWYHBZ-UHFFFAOYSA-N fluoroform;triphenylsulfanium Chemical compound FC(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ULHAZGTYRWYHBZ-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- DTQXTPZNDDSKIF-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-phenylethenol Chemical compound COC(=O)C(C)=C.OC=CC1=CC=CC=C1 DTQXTPZNDDSKIF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229940057061 mevalonolactone Drugs 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical class OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical class C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 150000002848 norbornenes Chemical class 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000000391 spectroscopic ellipsometry Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BIZVUECJOCNKDY-UHFFFAOYSA-N terephthalate;triethylazanium Chemical compound CC[NH+](CC)CC.CC[NH+](CC)CC.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 BIZVUECJOCNKDY-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- XTXNWQHMMMPKKO-UHFFFAOYSA-N tert-butyl 2-phenylethenyl carbonate Chemical compound CC(C)(C)OC(=O)OC=CC1=CC=CC=C1 XTXNWQHMMMPKKO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- MDTPTXSNPBAUHX-UHFFFAOYSA-M trimethylsulfanium;hydroxide Chemical compound [OH-].C[S+](C)C MDTPTXSNPBAUHX-UHFFFAOYSA-M 0.000 description 1
- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/006—Anti-reflective coatings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
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- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
合成例1
1.52gの4−ヒドロキシフェニル酢酸を40.37gのプロピレングリコールモノメチルエーテル(PGME)中に溶解した。このPGME溶液に、2.96gのトリヘキシルアミンを添加、混合した。
表1に例1〜15を列記する。これらの例は、全て、PGME中の原料溶液として製造されそして処方例に使用された塩である。これらは上に示した場合と同じように反応させたが、上記の処方例に使用すべき原料溶液としてPGME中の材料を残した。
PQMA/EAdMA(60/40)コポリマー(0.2218g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0665g)、トリエチルアミニウム4−ヒドロキシフェニルアセテート(0.0670g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0047g)を、13.57gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して反射防止組成物(B.A.R.C.)溶液を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.197g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0579g)、トリヘキシルアミニウム4−ヒドロキシフェニルアセテート(0.0991g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0058g)を、13.57gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.658g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.198g)、トリエチルアミニウム3−(4−ヒドロキシフェニル)プロピオネート(0.210g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0139g)を、40.73gのプロピレングリコールモノメチルエーテル、17.45gのプロピレングリコールモノメチルエーテルアセテート及び0.724gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.658g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.193g)、トリエチルアミニウム3−(4−ヒドロキシフェニル)プロピオネート(0.210g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0194g)を、40.74gのプロピレングリコールモノメチルエーテル、17.45gのプロピレングリコールモノメチルエーテルアセテート及び0.724gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/AdOMMA/EAdMA(55/20/25)ターポリマー(0.146g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.045g)、トリヘキシルアミニウム4−ヒドロキシフェニルアセテート(0.076g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0031g)を、13.64gのプロピレングリコールモノメチルエーテル、5.85gのプロピレングリコールモノメチルエーテルアセテート及び0.247gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/AdOMMA/EAdMA(55/20/25)ターポリマー(0.164g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.051g)、トリエチルアミニウム4−ヒドロキシフェニルアセテート(0.051g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0035g)を、13.64gのプロピレングリコールモノメチルエーテル、5.85gのプロピレングリコールモノメチルエーテルアセテート及び0.247gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.2258g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0634g)、3−ヒドロキシフェニル−N,N−ジメチルアミニウム4−ヒドロキシフェニルアセテート(0.0745g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0064g)を、13.57gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/AdOMMA/EAdMA(55/20/25)ターポリマー(0.171g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.050g)、ビス(3−ヒドロキシフェニル−N,N−ジメチルアミニウム)マロネート(0.044g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0050g)を、13.64gのプロピレングリコールモノメチルエーテル、5.84gのプロピレングリコールモノメチルエーテルアセテート及び0.25gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/AdOMMA/EAdMA(55/20/25)ターポリマー(0.160g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.049g)、3−ヒドロキシフェニル−N,N−ジメチルアミニウム4−ヒドロキシフェニルアセテート(0.057g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0047g)を、13.63gのプロピレングリコールモノメチルエーテル、5.84gのプロピレングリコールモノメチルエーテルアセテート及び0.25gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.232g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.068g)、ビス(3−ヒドロキシフェニル−N,N−ジメチルアミニウム)マロネート(0.0530g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0068g)を、13.58gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、感光性反射防止組成物を調製した。このB.A.R.C.溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.215g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.063g)、3−ヒドロキシフェニル−N,N−ジメチルアミニウム4−ヒドロキシフェニルアセテート(0.0745g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0064g)を、13.58gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、感光性反射防止組成物を調製した。このB.A.R.C.溶液を0.2μmミクロンフィルターに通して濾過した。
PQMA/EAdMA(60/40)コポリマー(0.232g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0683g)、ビス(3−ヒドロキシフェニル−N,N−ジメチルアミニウム)マロネート(0.0525g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0068g)を、13.58gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。
4−ヒドロキシスチレン/メチルメタクリレート(55/45)コポリマー(0.110g)、4−ヒドロキシスチレン/メチルメタクリレート(30/70)コポリマー(0.090g)、テトラメトキシメチルグリコールウリル(0.06g)、及びトリエチルアミニウム4−ヒドロキシベンゼンスルホネート(0.05g)を、9.825gのプロピレングリコールモノメチルエーテルアセテート、4.25gのプロピレングリコールモノメチルエーテル及び0.475gのγ−バレロラクトンの混合物中に溶解して、感光性反射防止組成物を調製した。このB.A.R.C.溶液を0.2μmミクロンフィルターに通して濾過した。
4−ヒドロキシスチレン/メチルメタクリレート(55/45)コポリマー(0.110g)、4−ヒドロキシスチレン/メチルメタクリレート(30/70)コポリマー(0.090g)、テトラメトキシメチルグリコールウリル(0.06g)、及び3−ヒドロキシフェニル−N,N−ジメチルアミニウム4−ヒドロキシベンゼンスルホネート(0.05g)を、9.825gのプロピレングリコールモノメチルエーテルアセテート、4.25gのプロピレングリコールモノメチルエーテル及び0.475gのγ−バレロラクトンの混合物中に溶解して、感光性反射防止組成物を調製した。この溶液を0.2μmフィルターに通して濾過した。
4−ヒドロキシスチレン/9−アントラセンメチルメタクリレート(80/20)コポリマー(0.2509g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0634g)、トリエチルアミニウム4−ヒドロキシフェニルアセテート(0.0304g)及びトリフェニルスルホニウムトリフルオロメタンスルホネート(0.0157g)を、15.9233gのプロピレングリコールモノメチルエーテル、7.3875gのプロピレングリコールモノメチルエーテルアセテート、1.1687gのγ−バレロラクトン及び0.7704gの乳酸エチルの混合物中に溶解して、感光性反射防止組成物を調製する。このB.A.R.C.溶液を0.2μmミクロンフィルターに通して濾過する。
PQMA/EAdMA(60/40)コポリマー(0.2394g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0718g)、ビス(トリエチルアミニウム)マロネート(0.0438g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0050g)を、13.57gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。このB.A.R.C.溶液をケイ素ウェハ上にコーティングし、そして処方及び露光例1に記載のように加工した。走査電子顕微鏡(SEM)を用いて、パターンを検査したが、125nmフォトレジスト/B.A.R.C.ライン(1:1)はスカムを示し、B.A.R.C.は、最適露光量(dose to print)(20mJ/cm2)で完全には溶解されなかった。
PQMA/EAdMA(60/40)コポリマー(0.2244g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0673g)、(トリエチルアミニウム)フェニルアセテート(0.0635g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0047g)を、13.57gのプロピレングリコールモノメチルエーテル、5.81gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。このB.A.R.C.溶液をケイ素ウェハ上にコーティングし、そして処方及び露光例1に記載のように加工した。走査電子顕微鏡(SEM)を用いてパターンを検査したが、125nmフォトレジスト/B.A.R.C.ライン(1:1)はスカムを示し、B.A.R.C.は、最適露光量(20mJ/cm2)で完全には溶解されなかった。
PQMA/EAdMA(60/40)コポリマー(0.2336g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0701g)、ビス(トリエチルアミニウム)テレフタレート(0.0514g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0049)を、13.58gのプロピレングリコールモノメチルエーテル、5.82gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。このB.A.R.C.溶液をケイ素ウェハ上にコーティングし、そして処方及び露光例2に記載のように加工した。走査電子顕微鏡(SEM)を用いてパターンを検査したが、125nmフォトレジスト/B.A.R.C.ライン(1:1)はフッティングを示し、そしてB.A.R.C.は、最適露光量(23mJ/cm2)で完全には溶解されなかった。
PQMA/EAdMA(60/40)コポリマー(0.2331g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0699g)、ビス(トリエチルアミニウム)シクロヘキサン−3,4−ジカルボキシレート(0.0521g)及びビス[トリス(4−ビニルオキシエトキシフェニル)スルホニウム]パーフルオロブタンジスルホネート(0.0049g)を、13.58gのプロピレングリコールモノメチルエーテル、5.82gのプロピレングリコールモノメチルエーテルアセテート及び0.241gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmミクロンフィルターに通して濾過した。このB.A.R.C.溶液をケイ素ウェハ上にコーティングし、そして処方及び露光例2に記載のように加工した。走査電子顕微鏡(SEM)を用いてパターンを検査したが、125nmフォトレジスト/B.A.R.C.ライン(1:1)はフッティングを示し、そしてB.A.R.C.は、最適露光量(23mJ/cm2)で完全には溶解されなかった。
PQMA/EAdMA(60/40)コポリマー(0.209g)、トリス(ビニルオキシブチル)シクロヘキサン1,2,4−トリカルボキシレート(0.0558g)、ビス(トリエチルアミニウム)マロネート(0.0323g)及びビス(トリフェニルスルホニウム)パーフルオロブタンジスルホネート(0.0023g)を、24.68gのプロピレングリコールモノメチルエーテル及び0.0203gのγ−バレロラクトンの混合物中に溶解して、反射防止組成物(B.A.R.C.溶液)を調製した。この溶液を0.2μmフィルターに通して濾過した。
Claims (14)
- 架橋剤、少なくとも一つの発色団基及び少なくとも一つのヒドロキシル及び/またはカルボキシル基を含むポリマー、及び添加剤を含む反射防止コーティング組成物であって、前記添加剤が次の構造1を有しかつ少なくとも一つのヒドロキシルアレーンの残基を含む、前記反射防止コーティング組成物。
- R1、R2及びR3のうちの少なくとも一つが、ヒドロキシアリール基である、請求項1〜4のいずれか一つに記載の組成物。
- 前記添加剤が、次の構造10:
のものであるか、あるいは
前記添加剤が、次の構造12:
のものである、請求項1〜5のいずれか一つに記載の組成物。 - R4が、ヒドロキシルアレーンの残基を含む、請求項2または6に記載の組成物。
- 発色団基が、置換されたフェニル基、置換されていないフェニル基、置換されたアントラシル基、置換されていないアントラシル基、置換されたフェナントリル基、置換されていないフェナントリル基、置換されたナフチル基、置換されていないナフチル基、酸素、窒素及び硫黄から選択されるヘテロ原子を含む置換されたヘテロ環式芳香族環、及び酸素、窒素及び硫黄から選択されるヘテロ原子を含む置換されていないヘテロ環式芳香族環、及びこれらの混合物から選択される、請求項1〜7のいずれか一つに記載の組成物。
- ヒドロキシル及び/またはカルボキシル基が、アクリル酸、メタクリル酸、ビニルアルコール、ヒドロキシスチレン類、ヒドロキシスチレンと1,1,1,3,3,3−ヘキサフルオロ−2−プロパノールを含むビニルモノマーとのコポリマーから選択されるモノマーから誘導される、請求項1〜8のいずれか一つに記載の組成物。
- 発色団基と、ヒドロキシル及び/またはカルボキシル基が、異なるモノマー性単位中における一つのモノマー性単位に存在する、請求項1〜9のいずれか一つに記載の組成物。
- Yが、次の構造2:
で表される、請求項1〜10のいずれか一つに記載の組成物。 - ポジ型画像の形成方法であって、
a)請求項1〜11のいずれか一つの底面光画像形成性反射防止コーティング組成物のコーティングを基材上に形成し;
b)反射防止コーティングをベークし;
c)底面コーティング上に上面フォトレジスト層のコーティングを供し;
d)フォトレジスト及び底面コーティング層を、同じ波長の化学線で像様露光し;
e)基材上のフォトレジスト及び底面コーティング層をポスト露光ベークし;及び
f)フォトレジスト及び底面コーティング層を水性アルカリ性溶液で現像して、それによってフォトレジスト及び反射防止コーティングフィルム中にパターンを形成する、
ことを含む前記方法。 - 反射防止コーティングが、フォトレジスト層のコーティングの前のベークステップの後に有機溶剤及び水性アルカリ性溶液中に不溶性になり、そしてフォトレジスト及び底面反射防止コーティング層の現像の前の化学線での露光の後に水性アルカリ性溶液中に可溶性になる、請求項12に記載の方法。
- ポジ型画像の形成方法であって、
a)請求項1〜11のいずれか一つに記載の反射防止コーティング組成物のコーティングを基材上に形成し;
b)反射防止コーティングをベークし;
c)底面コーティング上に上面フォトレジスト層のコーティングを供し;
d)フォトレジストを同じ波長の化学線で像様露光し;
e)基材上のフォトレジスト及び底面コーティング層をポスト露光ベークし;及び
f)フォトレジストを水性アルカリ性溶液で現像して、それによって反射防止コーティング上にフォトレジストパターンを形成する、
ことを含む、前記方法。
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